Chloroacetone → HCID 67092693, compound

HRID 1261831Notes

Reaction equation

HRID 1261831 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:17][C:18](=[O:20])[CH3:19].C(=O)([O-])O.[Na+]>O1CCOCC1.O>[CH3:2][O:3][C:4](=[O:15])[C@@H:5]([N:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:17][C:18](=[O:20])[CH3:19])[CH3:14]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 45489685Methyl N-benzyl-L-alaninate--hydrogen chloride (1/1)

Product 1

HCID 67092693HCID 67092693, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-benzylalanine methyl ester hydrochloride (1.00 g, 4.35 mmol), chloroacetone (1.21 g, 13.1 mmol), and sodium hydrogencarbonate (951 mg, 11.3 mmol) in 1,4-dioxane (11 mL) and water (1 mL) was heated at 70° C. for 2 days, then partitioned between EtOAc and 2 M aq. sodium carbonate solution. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (540 mg, 50%). Colourless oil, MS: 250.1 (M+H)+.

Workup

  1. custompartitioned between EtOAc and 2 M aq. sodium carbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-876957e2cc434ff89ae46209e44cb790
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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